Enantioselective Michael addition of 3-ethyl carboxylate substituted pyrazolones to 5-alkenyl thiazolones catalyzed by squaramide organocatalyst

Asymmetric Michael addition between 3-ethyl carboxylate substituted pyrazolones and 5-alkenylthiazolones catalyzed by a series of chiral bifunctional hydrogen bonding organocatalysts was investigated. Good yields (up to 96%) and excellent enantioselectivities (up to 99% ee) were achieved by using a squaramide containing piperidine group derived from (1S, 2S)-cyclohexanediamine. This strategy provides facile access to a diverse library of thiazole-pyrazolone derivatives with potential bioactivity.